Actein

CAS# 18642-44-9

Actein

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Chemical structure

Actein

3D structure

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Chemical Properties of Actein

Cas No. 18642-44-9 SDF Download SDF
PubChem ID 6537491 Appearance White powder
Formula C37H56O11 M.Wt 676.9
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Shengmating
Solubility Soluble in acetonitrile; practically insoluble in water
Chemical Name [(1S,1'R,2S,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-2-hydroxy-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
SMILES CC1CC2(C3C(O3)(C(O2)O)C)OC4C1C5(C(CC67CC68CCC(C(C8CCC7C5(C4)C)(C)C)OC9C(C(C(CO9)O)O)O)OC(=O)C)C
Standard InChIKey NEWMWGLPJQHSSQ-PSDKAYTQSA-N
Standard InChI InChI=1S/C37H56O11/c1-17-12-37(29-34(7,47-29)30(42)48-37)46-20-13-32(5)22-9-8-21-31(3,4)23(45-28-27(41)26(40)19(39)15-43-28)10-11-35(21)16-36(22,35)14-24(44-18(2)38)33(32,6)25(17)20/h17,19-30,39-42H,8-16H2,1-7H3/t17-,19-,20+,21+,22+,23+,24-,25+,26+,27-,28+,29-,30+,32+,33-,34+,35-,36+,37-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Actein

The roots of Cimicifuga racemosa

Biological Activity of Actein

Description1. Actein has a stimulatory effect on osteoblastic bone formation or has potential activity against osteoporosis, it also can prevent oxidative damage to osteoblasts in osteoporotic patients. 2. Actein's ability to pathways involved in lipid disorders and carcinogenesis may make it a new agent for preventing and treating these major disorders. (1) Actein has been shown to inhibit the proliferation of human breast cancer cells, by altering the activity of the ER IP3 receptor and Na,K-ATPase, inducing calcium release and modulating the NF-κB and MEK pathways. (2) Actein reduces free fatty acid and cholesterol content in the liver by 0.6-fold at 24 h and inhibites the growth of human HepG2 liver cancer cells.
TargetscAMP | TNF-α | NF-kB | Sodium Channel | ATPase | Potassium Channel | MEK | p53 | Akt | P450 (e.g. CYP17)

Actein Dilution Calculator

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Preparing Stock Solutions of Actein

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.4773 mL 7.3866 mL 14.7732 mL 29.5465 mL 36.9331 mL
5 mM 0.2955 mL 1.4773 mL 2.9546 mL 5.9093 mL 7.3866 mL
10 mM 0.1477 mL 0.7387 mL 1.4773 mL 2.9546 mL 3.6933 mL
50 mM 0.0295 mL 0.1477 mL 0.2955 mL 0.5909 mL 0.7387 mL
100 mM 0.0148 mL 0.0739 mL 0.1477 mL 0.2955 mL 0.3693 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Actein

Actein inhibits the Na+-K+-ATPase and enhances the growth inhibitory effect of digitoxin on human breast cancer cells.[Pubmed:18755149]

Biochem Biophys Res Commun. 2008 Oct 31;375(4):608-13.

The Na+K+-ATPase is a known target of cardiac glycosides such as digitoxin and ouabain. We determined that the enzyme also is a target of the structurally-related triterpene glycoside Actein, present in the herb black cohosh. Actein's inhibition of Na+-K+-ATPase activity was less potent than that of digitoxin, but Actein potentiated digitoxin's inhibitory effect on Na+-K+-ATPase activity and MDA-MB-453 breast cancer cell growth. We observed different degrees of signal amplification for the two compounds. Actein's inhibitory effect on ATPase activity was amplified 2-fold for cell growth inhibition, whereas digitoxin's signal was amplified 20-fold. Actein induced a biphasic response in proteins downstream of ATPase: low dose and short duration of treatment upregulated NF-kappaB promoter activity, p-ERK, p-Akt and cyclin D1 protein levels, whereas higher doses and longer exposure inhibited these activities. Actein and digitoxin may be a useful synergistic combination for cancer chemoprevention and/or therapy.

Actein induces calcium release in human breast cancer cells.[Pubmed:23939423]

Fitoterapia. 2013 Dec;91:28-38.

BACKGROUND: The triterpene glycoside Actein from the herb black cohosh preferentially inhibits the growth of breast cancer cells and activates the ER stress response. The ER IP3 receptor and Na,K-ATPase form a signaling microdomain. Since Actein is lipophilic, its action may be limited by bioavailability. PURPOSE: To develop Actein to prevent and treat cancer, we examined the primary targets and combinations with chemotherapy agents, as well as the ability of nanoparticles to enhance the activity. MATERIALS AND METHODS: To reveal signaling pathways, we treated human breast and colon cancer, as well as 293T and 293T (NF-kappaB), cells with Actein, and measured effects using the MTT, luciferase promoter, Western blot and histology assays. To assess effects on calcium release, we preloaded cells with the calcium sensitive dye Fura-2. To enhance bioavailability, we conjugated Actein to nanoparticle liposomes. RESULTS: Actein strongly inhibited the growth of human breast cancer cells and induced a dose dependent release of calcium into the cytoplasm. The ER IP3 receptor antagonist heparin blocked this release, indicating that the receptor is required for activity. Heparin partially blocked the growth inhibitory effect, while the MEK inhibitor U0126 enhanced it. Consistent with this, Actein synergized with the ER mobilizer thapsigargin. Further, Actein preferentially inhibited the growth of 293T (NF-kappaB) cells. Nanoparticle liposomes increased the growth inhibitory activity of Actein. CONCLUSIONS: Actein alters the activity of the ER IP3 receptor and Na,K-ATPase, induces calcium release and modulates the NF-kappaB and MEK pathways and may be worthwhile to explore to prevent and treat breast cancer.

Actein activates stress- and statin-associated responses and is bioavailable in Sprague-Dawley rats.[Pubmed:19527300]

Fundam Clin Pharmacol. 2009 Jun;23(3):311-21.

The purpose of this study was to assess in rats the pharmacological parameters and effects on gene expression in the liver of the triterpene glycoside Actein. Actein, an active component from the herb black cohosh, has been shown to inhibit the proliferation of human breast cancer cells. To conduct our assessment, we determined the molecular effects of Actein on livers from Sprague-Dawley rats treated with Actein at 35.7 mg/kg for 6 and 24 h. Chemogenomic analyses indicated that Actein elicited stress and statin-associated responses in the liver; Actein altered expression of cholesterol and fatty acid biosynthetic genes, p53 pathway genes, CCND1 and ID3. Real-time RT-PCR validated that Actein induced three time-dependent patterns of gene expression in the liver: (i) a decrease followed by a significant increase of HMGCS1, HMGCR, HSD17B7, NQO1, S100A9; (ii) a progressive increase of BZRP and CYP7A1 and (iii) a significant increase followed by a decrease of CCND1 and ID3. Consistent with Actein's statin- and stress-associated responses, Actein reduced free fatty acid and cholesterol content in the liver by 0.6-fold at 24 h and inhibited the growth of human HepG2 liver cancer cells. To determine the bioavailability of Actein, we collected serum samples for pharmacokinetic analysis at various times up to 24 h. The serum level of Actein peaked at 2.4 microg/mL at 6 h. Actein's ability to alter pathways involved in lipid disorders and carcinogenesis may make it a new agent for preventing and treating these major disorders.

Actein isolated from black cohosh promotes the function of osteoblastic MC3T3-E1 cells.[Pubmed:24552231]

J Med Food. 2014 Apr;17(4):414-23.

Actein, isolated from black cohosh, was subjected to in vitro experiments to investigate its functional bioactivities in osteoblastic MC3T3-E1 cells. Actein caused a significant elevation of alkaline phosphatase activity, collagen synthesis, osteocalcin production, mineralization, and glutathione content in the cells, suggesting that Actein has a stimulatory effect on osteoblastic bone formation or has potential activity against osteoporosis. We investigated the protective effects of Actein on mitochondrial electron transport inhibitor, antimycin A induced toxicity in osteoblastic MC3T3-E1 cells. Exposure of MC3T3-E1 cells to antimycin A caused significant decrease in cell viability and mineralization. However, pretreatment with Actein prior to antimycin A exposure significantly reduced antimycin A-induced cell damage by preventing mitochondrial membrane potential dissipation, complex IV inactivation, cardiolipin oxidation, ROS release, and nitrotyrosine increase, suggesting that Actein may be useful for protecting mitochondria against a burst of oxidative stress. In addition, Actein increased the phosphorylation of CREB (cAMP-response element-binding protein) inhibited by antimycin A and decreased the production of TNF-alpha induced by antimycin A. These findings suggest that Actein could prevent oxidative damage to osteoblasts in osteoporotic patients.

Description

Actein is a triterpene glycoside isolated from the rhizomes of Cimicifuga foetida. Actein suppresses cell proliferation, induces autophagy and apoptosis through promoting ROS/JNK activation, and blunting AKT pathway in human bladder cancer. Actein has little toxicity in vivo.

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